Interesting thread, and I'm sure several folks will benefit.
We're home now, but with the exception of about six weeks (two trips) in Florida earlier this year - 2014 has mostly been a non-boating year for us. That will probably change in 2015.
Our current (very rough) plan is to launch the boat somewhere south of Jacksonville (FL) in about April(?) and cruise 'North. We don't know for how-long, but since we're both very comfortable aboard it'll probably somewhere in the 3-6 month range. We don't know for sure where we'll go, exactly when we'll leave, or exactly how long we'll be aboard -- but we'll figure it out as we go. The Important part will be that we'll be cruising together!
At this point I can't see us (ever) owning a boat that doesn't fit on a trailer.
Some of the cruising amenities and lessons we've learned:
* The WAECO/dometic freezer GREATLY enhances our meal planning (and permits me to have ice cubes for my evening Scotch.
* As an experiment we rigged a 1/8" nylon cord across two of the three bows beneath the camper canvas; now we have our own clothesline. We use it daily.
* Redundancy (within limits) can be very useful. We now use a small Coleman propane burner for routine cooking. It's cheap, fast, convenient, portable (works well in the cokpit or on a dock) and serves as a backup to the Wallas (which will eventually die one of these days). We also like to keep a single burner hotplate on the boat for those time's we're at a marina. We also carry a fan that operates on 12V/110 to enhance ventilation when necessary. When it's cold we use a 110V heater called a "Big Heat." It's easy to use if at a marina.
* The iPad works so well for navigation and other chores we couldn't live without it. We also get good use out of our iPhones, XM radio, and a plethora of various (re)charging wires. ...oh, and don't forget a small inverter.
* Installing a couple of extra 12V sockets in the cockpit has been Very handy.
* LED lights in the cabin help (be sure to get the "warm white" color, not the bluish white version).
* spend some time figuring out how you want the galley layed-out. We probably all take too much in that regard. (DD's comment was right-on.)
* On such a small boat space is at a premium so prior planning will pay (big) dividends.
* We prefer to anchor-out, but will stay at a marina if the situation/locale/price are in alignment. Staying on anchor is actually better if it's warm (with any breeze the boat will weather vane into the breeze and provide some flow-through cooling.
* A nice, stable candle on the dinette can add 'atmosphere!

* Use ActiveCaptain. I say again: USE ACTIVECAPTAIN!!
* Autopilot is Fantastic (and makes displacement cruising much easier).
* I'm sure the 'list is endless!
All this fans my let's-go-Cruising desire!
Best,
Casey&Mary